The total synthesis of the polypyrrolindoindoline alkaloid quadrigemine H is described. The synthetic plan utilizes the intramolecular asymmetric Heck chemistry to construct the four quaternary carbon centers in the molecule. Members of the polypyrrolindoline alkaloids demonstrate a wide range of biological activity, including cytotoxicity, anti-viral, anti- bact3rial, anti-fungal, and anti-canndidal activities. The methodology to be developed can be readily adapted to synthesize the whole family of these alkaloids.